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Search results; Over 1,000 homes in Madison

Top guest favourite
Farm stay in Madison
Madison Nature Getaway
1 bedroom, 2 beds, 1 private bathroom
19–24 Jul
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4.98 out of 5 average rating, 225 reviews
Guest favourite
Home in Woolford
Gorgeous Waterfront, Beach, Pool, Pets- 7 Bd /5ba
4.98 out of 5 average rating, 87 reviews, 7 bedrooms, 13 beds, 5 bathrooms
29 Aug – 3 Sept
Guest favourite
Home in Woolford
"Endless Summer" on the Chesapeake!
5.0 out of 5 average rating, 5 reviews, 4 bedrooms, 7 beds, 2.5 bathrooms
17–22 Aug
Guest favourite
Place to stay in Cambridge
Wye Three Oaks
4.96 out of 5 average rating, 96 reviews, 2 bedrooms, 4 beds, 1 bathroom
25–30 Jul
Top guest favourite
Home in Woolford
Starboard on McKeil Point, w/heated pool & hot tub
4.99 out of 5 average rating, 141 reviews, 6 bedrooms, 11 beds, 4.5 bathrooms
5–10 Sept
Top guest favourite
Home in Madison
Madison Bay Club House
5.0 out of 5 average rating, 50 reviews, 3 bedrooms, 7 beds, 2.5 bathrooms
27 Aug – 1 Sept
Top guest favourite
Home in Cambridge
Relaxing Retreat on the Hudson
4.96 out of 5 average rating, 73 reviews, 5 bedrooms, 5 beds, 2 bathrooms
24–29 Aug
Top guest favourite
Home in Cambridge
Sunset Breezes - quiet waterfront retreat
4.99 out of 5 average rating, 218 reviews, 3 bedrooms, 5 beds, 2 bathrooms
23–28 Aug
Top guest favourite
Home in Woolford
Newly Renovated Modern 3 bed 2 bath Water Front
5.0 out of 5 average rating, 246 reviews, 3 bedrooms, 3 beds, 2 bathrooms
19–24 Jul
Top guest favourite
Home in Cambridge
Serene getaway with great waterfront views!
5.0 out of 5 average rating, 41 reviews, 3 bedrooms, 5 beds, 2.5 bathrooms
23–28 Jul
Top guest favourite
Home in Cambridge
Chesapeake Sunset Cottage
4.97 out of 5 average rating, 104 reviews, 2 bedrooms, 2 beds, 2 bathrooms
31 Aug – 5 Sept
Home in Cambridge
Family and Pet-Friendly, Waterfront with Pier
4 bedrooms, 5 beds, 1.5 bathrooms
27 Sept – 2 Oct
Guest favourite
Home in Cambridge
280 Acre Waterfront Estate With Dock and Pool
5.0 out of 5 average rating, 11 reviews, 5 bedrooms, 10 beds, 6 bathrooms
1–8 Aug
Top guest favourite
Home in Cambridge
Modern Chesapeake Waterfront - Heated Pool - Dock
5.0 out of 5 average rating, 8 reviews, 5 bedrooms, 8 beds, 3.5 bathrooms
20–25 Sept
Superhost
Home in Dorchester County
Rippling Waters on Fishing Creek
3 bedrooms, 4 beds, 1.5 bathrooms
26–31 Jul
Guest favourite
Cabin in Lusby
Waterfront Log Cabin: Deep Work & Nature Retreat
5.0 out of 5 average rating, 5 reviews, 3 bedrooms, 4 beds, 2 bathrooms
26–31 Jul
Top guest favourite
Home in Woolford
Waterfront Getaway with Dock
4.94 out of 5 average rating, 187 reviews, 3 bedrooms, 4 beds, 2 bathrooms
23–28 Aug
Top guest favourite
Home in Taylors Island
Holliday House
5.0 out of 5 average rating, 22 reviews, 3 bedrooms, 6 beds, 1.5 bathrooms
21–26 Jul
Superhost
Home in Woolford
Eastern Shore Waterfront-Pier, Kayaks, FirePit
2 bedrooms, 4 beds, 1 bathroom
26–31 Jul